Background: Urethroplasty is the gold standard treatment procedure for male patients with urethral stricture and is becoming increasingly popular among urologists worldwide. Procedure success rates have risen with increased experience. Aims: Here we aimed to examine the results of urethroplasty in challenging cases of urethral stricture and its effect on sexual function. Patients and Methods: Data were collected retrospectively from the patients who had undergone urethroplasty after multiple failed direct vision internal urethrotomy (DVIUs) from 2017 to 2020. All patients were monitored for a minimum of 12 months. Outcomes of urethroplasty were analyzed according to stricture location, length, and the number of prior DVIUs. Penile length and sensation, erectile, and ejaculatory function of the patients were evaluated pre- and postoperatively. Results: The patient cohort consisted of 36 males with a mean age of 63 ± 3.2 years. The most prevalent stricture etiology was iatrogenic (83%). Patients who underwent three or more DVIUs before urethroplasty and stricture length >4 cm were included in the analysis. Accordingly, the overall success rate was 83% (30/36). When the success rate and the IIEF5 scores were assessed separately, there was no significant relationship between the number of DVIUs (P > 0.05). Similarly, no significant relationship was also found with the stricture length (P > 0.05). Conclusion: Appropriate and correctly applied surgical technique does not impair sexual activity, even in patients with severe urethral stricture, regardless of the length or location of the stricture and the number of prior endoscopic procedures.